The prospect of radically changing teaching and learning by issuing a laptop computer to every student and teacher is an exciting one, but it carried big risks and would take time and thorough planning to execute well. But even thorough planning can't prevent the unanticipated. In this article, the author counts six major surprises during his time implementing a 1-to-1 initiative in the Pascack Valley Regional High School District in Montvale, New Jersey. The district serves more than 2,100 students in grades 9-12.